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The Moneyist: ‘I spend $600 a month taking women out for dinner and drinks’: Does the man always have to pick up the check on a first date?

Dear Quentin,

I am a single 38-year-old man living in the Southwest, and I have reached my breaking point.

I spend my hard-earned money taking women out for dinner and drinks who I’ve met on Tinder, only to be ghosted by the second or third date. Is taking a woman out for coffee on a first date acceptable? And can I just pay for my own? You don’t get much change out of $10 at Starbucks

these days, and I’m tired of just throwing my cash around on other people’s social lives. 

At this point in the game — and it does feel like a game — I feel like I’m being taken advantage of by the women who agree to meet me on a date. If they’re not serious, then why do they agree to be taken out for dinner? A bottle of wine can cost upwards of $45.

I am a gentleman. I hold the door for women, I stand up when a lady enters the room, and I pick up the check. But I’m spending upwards of $600 a month on dates, and it’s eating into my other living expenses. 

When did men have to pay for everything? When did dating have to be so expensive? Is coffee acceptable? Can I buy my own?

Thirty-something, Single and Aggravated

Dear TSA,

Yes, you can go for coffee, and yes, you can buy your own. You don’t have to pay for dinner every single time. Chivalry does not have to mean spending $600 a month on a merry-go-round of dating. Silicon Valley has commodified people’s romantic lives, and given the sheer number of singletons meeting, it no longer makes financial sense to always be the one to pay. 

In this poll carried out by YouGov, more than one-third of respondents said they use dating apps so they have something to do — that is, they have incorporated dates into their social calendar as an activity, like going to the cinema or playing pickleball. More than a quarter of respondents said they use apps to have casual sex. Men (36%) were more likely than women (14%) to say this. 

Twenty years ago, you might have gone on two or three dinner dates a month with the same person. But today’s economic conditions no longer support the old-fashioned notion that men should always pick up the bill for pre-dinner drinks, dinner and wine. It’s not feasible, especially with inflation at a 40-year high and wage growth struggling to catch up.

There is hope. Most people in the YouGov poll said they were on a dating site to find an exclusive romantic partner (50% of men vs. 59% of women). Other reasons include making friends, meeting non-exclusive romantic partners, and boosting their self-esteem. (Who doesn’t like to get a right-swipe to start their day and a DM saying how pretty or handsome they are?) 

“‘Today’s economic conditions no longer support the old-fashioned notion that men should always pick up the bill.’”

All of that adds up to a lot of socializing under the auspices of mating rituals — where the man always pays — that really went out of fashion long before Hinge, OKCupid, Tinder, Bumble,

and Grindr came on the market. I’ve received a lot of letters like yours in recent times, including this one about when it’s not OK to have your partner pay for your wine.

A recent survey by LendingTree, a personal-finance site, found that one in five Americans are dating less due to inflation. Despite this, more than half of men (54%) say the man should pay for the first date. What’s more, more than one-third of singletons want to know how much their partner makes, while just over one-quarter would like to have that information before they go on a date.

Daters said they spend an average of $91 at most on a date, but if you’re going on half a dozen dates a month, that adds up. Men say they spend $81 on average on a date; women say they spend $104. Given these numbers, which are likely far higher in expensive cities like New York and L.A., walks in the park (during daylight hours) and coffee are a reasonably prudent start.

“‘If you have a real connection with someone and believe that you will likely see each other again, take her to your favorite restaurant and push out the boat.’”

But you must take responsibility for your own dating life too. For safety and fairness, it’s always a good idea to talk on the phone to get an idea of the other person’s personality and values. If they talk about themselves for half an hour without asking you one question, you know they’re not for you. If they are inappropriate or have nothing to say, skip coffee and dinner. 

If your prospective date is still angry about their ex, and wants to list all of the reasons why and how they done ’em wrong, they are not truly available — in fact, they may as well be still in the relationship. They’re not ready to date, and it’s not a good sign if your Tinder date believes all the blame lies with their former love. 

In other words, be more judicious about whom you take for dinner or drinks or even coffee, and listen to your instincts, as they will inevitably be correct. There’s one thing that will cost you more than $600 a month on dating, and that’s your time. It’s an ever-diminishing commodity: The older we get, the less of it we have, and even a coffee date will take an hour out of your day.

If you have a real connection with someone and believe that you will more likely than not see each other again, take her to your favorite restaurant and push out the boat. But taking date after date for dinner without any real knowledge of the person’s values, politics or personality — or if they are even emotionally ready for a relationship — will drain your finances for years to come.

Check out the Moneyist private Facebook group, where we look for answers to life’s thorniest money issues. Readers write in to me with all sorts of dilemmas. Post your questions, tell me what you want to know more about, or weigh in on the latest Moneyist columns.

The Moneyist regrets he cannot reply to questions individually.

By emailing your questions, you agree to having them published anonymously on MarketWatch. By submitting your story to Dow Jones & Co., the publisher of MarketWatch, you understand and agree that we may use your story, or versions of it, in all media and platforms, including via third parties.

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